A Sissy in the 22nd Century Pt. 05

Preface

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society's needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other's fundamental desires. This is achieved through the medium of an overruling system of artificial intelligences and mathematical algorithms which record vast amounts of data about each individual from the moment they are born; working out precisely where they will most comfortably fit into the lives of everyone else.

Medical science has also made great leaps, to the degree in which the Grand Algorithm can manipulate hormone provision and expression in all those under its control... Shaping their bodies and minds to perfectly fit the role it determines they are destined to fill. Citizens age slowly and rarely suffer any sort of malady, with immortality being considered a very real possibility in the next decade or so. Ideas like gender division are considered childish and old fashioned, with what genitalia and pronouns an individual uses dependant more on the lifestyle they lead than whatever was attached when they were born.

There are still inequalities and divisions within society though. Having emerged from the cocoon of free market capitalism, society is still very much tiered by class and overshadowed by corporate elitism... with the commodities sold simply having changed entirely toward 'entertainment' in one fashion or another. The rich are seemingly deemed fit to stay so by the Algorithm, the middle classes content enough to spend their entire lives devoted to any perversion that might take their fancy. This self-centred outlook leaves little interest in raising a family, so any children they do produce are generally given over to group 'Homes' wherein they are looked after and raised by those who have been determined to actually enjoy parenting. These young men and women are, of course, then sorted into roles that provide for their progenitors desires... thus continuing the cycle.

The story of Jesse, 1st class sissy-slutwife in training, continues apace. Having had a traumatic first few days of submissive education... our femboy heroine is already beginning to lose sight of his life before all this. Hearing the tales and daily lives of his fellow submissives, it almost seems a guilty selfishness to complain about his lot. From specifically-tailored outfits to neighbours willing to use him as 'massage-practice', his place in society really seems to be settling into its own form of luxury... Whether that pampering is ultimately all for the benefit of others, or not.

Chapter 1: Offered Seats

The next morning, Jesse woke up in Betsy's bed, wrapped up in the girl's protective embrace. He felt warm, and safe, and strangely well rested. A perpetually light sleeper, the sissy was used to waking up somewhere near a thousand times a night: needing to creep through the corridors in his nightie to the communal toilets, or just lie staring at the ceiling in a cloud of swirling thoughts until his roommate's snores lulled him back to the respite of oblivion. Alone, in his own bed, he would often shrivel into the next morning in a ball of unreleased tension. As if he'd spent every dream sprinting between shadows and squeezing into cracks too small for even his slight frame to hide in. No such aches and creaks came from his bones today though... leaving the idea that perhaps there had been more to Cynthia's massage than just her own gain, after all. He got up and dressed, admiring the cut of his slim figure in the tall mirror of their shared wardrobe.

Somewhere along the line... he had got used to seeing himself in the smart-but-skimpy lines of his new school uniform. The amount of his smooth, pale flesh on display hardly even registered. Nor the absence of any underwear, pre-worn or otherwise. He stood on his tall, blocky heels with fairly practised ease, even trying out a few of the 'resting poses' Ms Durian had suggested he learn to make a habit of... 'to subtly show off what you've got'. It seemed a little corny to be told how he even had to stand around doing nothing, in order to be more pleasing upon his future master's eyes. But then he remembered just how pristine and graceful every movement the seniors who had welcomed them into the school made was, and couldn't help but dream of having such eye-dragging poise. Would the school begin handing out thinner and more dainty heels soon, now that most of the class had got used to these ones?

The sissy couldn't help but feel he was wearing the equivalent of training-wheels currently, and had a sudden urge to prove he could do better. He carefully applied some lipstick, foundation and eyeliner... trying his best to meet the standard that Betsy seemed to so-easily achieve. Most of the hickeys and bite-marks that weren't hidden by his blouse and skirt had faded actually, except for one or two large ones on his inner thighs and neck. He couldn't do much about his thighs, but found a thin silk scarf that Betsy had bought him once. Wrapping it around his neck and matching it with the colour of his knee-socks and hairbands today made him feel like he was making the outfit his own at least a little bit, not just what he was forced to wear. The lauded beauty of a boy had never really seen what everyone else seemed to make such a fuss about in his looks... but today he felt tentatively good about his outward appearance.

Stepping onto the Maglev after breakfast, the sun was still shining upon this last day of his first week in specialised education. He even managed to find a space for his bare little ass to plonk itself without any requirement that he balance precariously upon the knee and inevitable erection of a stranger. So pleased was the sissy with how the day was shaping up that he even offered that same seat over when a wrinkled old lady clambered wearily on at the next stop. She smiled and thanked him dearly, settling down with a glint in her eye while he hung on to the silver pole nearby. To be honest, Jesse was rather amazed by the sight of her himself. It was rare to actually see someone who looked old these days, being as there were some centenarians these days who could still appear twenty if they felt like it. Those who were actually beyond the reach of the algorithm's help tended to not be in any state to walk around either.

"That was very kind of you dear..." A voice like crackling autumn leaves told him. "But, I recognise that uniform... isn't there something else you're supposed to say to me?"

She smiled up at him in a particularly encouraging and unthreatening way, making Jesse blush just with the embarrassment that he hadn't even considered she should count among 'everyone' in the rules he was supposed to follow.

"Oh, ermm... yes! Sorry... Hello Ma'am, my name is Jesse. How may I service you?"

The aged creature's face cracked even wider at the lilting, stumbling tones of the polite, little sissy. She pulled out a flexitab from her large and jangling handbag and began pawing at it with just a hint of inexperienced confusion.

Chapter 2: Supporting the cause

"Let's see dear... I'm still not very good with these things... Could you help me?"

Jesse was drawn in to help the little old lady connect her device to his own collar. Which was not the sort of tech support he'd ever thought he'd have to do. While he did so, immediately bringing up several images of him sliding in and out of Lizzy, the woman just kept on chattering away:

"We sent one of my granddaughters off to Madame Stanfield's, I remember. She was going spare, after all... all the inheritance had been shared out already. Was a right little terror too, before she entered the academy. Always running off to hang around with dropouts and drug dealing thugs, or distracting any workmen who came to the house. Once even refused to eat her meals so long she nearly got pregnant... luckily the algorithm caught it in time or our problems would have multiplied!"

Jesse was beginning to remove the 'nice' from his mental assessment of this wrinkled, old creature. She talked about her own kin with a detached callousy that he simply hadn't encountered before, though he'd been hearing whispers that this was what rich people were like for years.

"That headmistress of yours sorted her out in no time, though. It warmed my heart every time I heard her greet one of her father's business partners with that 'may I service you?' line... it helped secure an awful lot of good deals for him. He even managed to trade her off for a very good share in one of our competitors in the end. Who'd have thought the runt of the litter could be so much use, eh? That's why I always try to help out if I ever see one of you girls in your smart, little uniforms..."

The woman had taken her portable device back now, and was scrolling through its list of options while sucking on a chunk of hard candy she seemed to have produced from nowhere. Jesse just had to wait in trepidation while the carriage swayed and he wondered what on earth this crone was going to make him do for her.

"Ah, there we go! She exclaimed, jabbing 'confirm purchase' with a relish. Now, you just pull out that little sausage you're hiding and stroke it for me. We'll see how far you can get with it before you have to get off."

Jesse glanced up and down the semi-crowded carriage, commuters of various shapes and sizes clogged the seats and passages. Most minding their own business for the moment. He had no choice anyway... the choker around his neck had buzzed to confirm the lady's demands. With his accustomed flush of bright-red cheeks, the sissy lifted up the front of his skirt and took hold of his penis. For a while he didn't think he was going to 'get anywhere' with it at all. Trying to stroke life into its tiny softness in the broad daylight of a Friday morning's transport system, while a seated hag watched intently and sucked loudly upon her boiled sweet. Yet, the embarrassment of the moment and innate need to please even those he'd taken an immediate disliking to, soon got blood pumping where it should.

It was a particularly strange and difficult thing to do: masturbating for the casual entertainment of someone else... even without the added pressures of a train full of side-line observers and the disgusting slurping noises his customer was making. Jesse squirmed through the horrendous mechanics of it, turned almost equally on and off by his own humiliated awkwardness. The old lady lapped up the knees-locked sight of him, desperately trying to just get this over with but also dreading the thought of what might happen if he went too far.

As the sleek vehicle slipped along at breakneck speed, its internal carriages only swaying ever so slightly... Jesse began to think he might make it to his station without spilling his load. Surely his short-rental mistress couldn't complain if he did exactly what she wanted, but just never quite made it to orgasm? He was buoyed by the general disinterest the rest of the passengers seemed to be giving him. Just another slutty schoolboy jacking off in public for pocket change... they must have seen it all before. The warmth and confidence he had felt this morning still hadn't faded. This was just another shape of the new morning routine, like how he was beginning to get used to the idea that a stranger's lap was a more appropriate seat for one such as him. Nothing to get upset over...

A flash of blinding light crossed his vision. Simultaneous with a jarring wave of pins and needles which launched itself up and down his spine. In shock and horror he looked down and spotted the old lady holding her flexitab again, seemingly this time with an entirely able grip over its functions. With an unrestrainable, girly squeal the sissy felt all his internal buttons pushed at once and pure pain and pleasure overwhelm him. His little cock became a fountain almost immediately, splattering the well dressed woman with spurt after spurt of shaken-loose semen. Until everything he had had been released, and Jesse dropped to his trembling knees... Lightning still lodged in his spine and the old lady's triumphant smile seared into his mind.

Chapter 3: Cheered on out

It was the cheer that went up and down the carriage... that really shook Jesse. He could hear it still ringing in his ears as she made him clean her off. Licking up what drips of his own expulsion he could find, on the leathery skin of her cheeks and breastbone, or the actual leather of her boots. He did it wordlessly and in a daze... Only just managing to scurry out the door when his station arrived. Every day, he caught the same train at the same time. Already he was beginning to recognise some of the regular faces who shared that commute... and now surely each and every one was going to remember having seen him blow his load all over a wrinkled old witch perhaps five or six times his age. The utter debasement of how she had tricked him hollowed out his soul... Along with the promise she had whispered in his ear before he left:

"There now, Sweetums... That'll win you a few more interested parties. I catch this train every week or so. Perhaps we'll get them to join in a little next time, to? I know a bottom that needs a few more spankings when I see one... You be good in school until then, though."

She had reached around to squeeze his ass at that, then patted it on its way. Leaving Jesse to walk onwards with the feel of that wrinkled touch upon his backside and the deflating sense of post-orgasm shame still dripping down his inner leg a little. Except... He shouldn't feel ashamed, should he? All that had just happened was what was supposed to. He had simply earned a little extra towards his tuition and presumably bumped his grades up a little by letting a valued supporter of the school have a bit of fun with him. Desperately searching for that body of confidence he had felt this morning, Jesse tried to see it like Betsy would. Like Madame Stanfield and the whole damn world wanted him to: He was a sissy slut and she had just treated him the way sluts should be treated. He should be proud to walk into school with reddened ass-cheeks and a sticky, little cock... He only wished that was how he felt, when he finally climbed the entrance steps.

Suzy and co were waiting for him. Each one ready with a willing tongue to shove down his throat in greeting. Once again, the troubled femboy found himself brought back up to spirits by their open camaraderie. The rule that they all had to kiss one another in greeting was already proving to be a popular one. The commanded necessity of it seemed to open up the way for them to just feel more comfortable around each other's bodies. It was just a gentler juxtaposition of that same conundrum that Jesse was battling with. His classmates were all just playthings too, after all. Why should any of them feel awkward roaming hands across each other's flaunted curves, or showing their affection romantically and erotically? Overt sexuality was their shape and purpose... there were no lines to be crossed in that.

While they were all still milling around waiting for the first bell to ring, Jesse noticed some further movement to one side of the room. Another of the seniors he recognised from his first day was splayed out across a side table probably placed there for this very reason. It was the green-haired, punkish-looking hermaphrodite; though this time free of all her leather straps and dressed only in a full-body fishnet stocking... with carefully placed tears in all the right places. She was being driven into at each end by two workmen in dirty boiler-suits: chatting away amiably over the wet, slapping and gurgling sounds of their efforts. Jesse became fascinated by the bulge he could see forming in the senior's neck as she simply lay back and took the entire lengths of both men, entirely unfazed and unchoked by their girths. He found himself drifting a little closer, catching glimpses of their conversation:

"See I told you these school jobs were the best! Ain't nobody grows a good little fucktoy like Scary Miss Stanfield does..."

"I still don't see why they need all this fancy stuff... or to call us out for jobs the robots could do, just to teach all these hussies how to suck a cock better... We could be doing this with Sally, back at the office. Sure, she's getting a bit loose around the fuckholes these days... but it would mean I didn't have to watch that bouncing around every time I push in!"

The second worker looked pointedly at the student's large, but flaccid cock which was indeed flapping a little... here and there... as he pumped away next to it. It clearly made him uncomfortable, for some reason Jesse couldn't quite fathom.

"That's 'cause you got no class. You don't even know perfectly-trained fuckmeat when you're balls deep in it. Sally's barely even 3rd class these days... lolling around like a wet sponge while you screw her, barely able to focus on anything except the next cock waiting in line for their break. Boss's been trying to trade her on for something fresher for months now, but even then it'll be some second-hand whore who barely got outta Basic before they tied her up under some office-drone's desk."

The man pulled his penis out from the depths of the senior's throat, letting her catch a few, rasping breaths while he slapped her across the face with it.

"While this is the kinda toy they'll send right to the top floor of that skyscraper. Where they'll balance glasses of champagne worth more than your year's paycheck on her, and seal deals selling off stocks in a thousand more Sally's by pissing it back into her. We're getting a chance to stick our dicks in fucking caviar, son... Savour the chance while you've got it..."

At that moment, the bell rang... and Jesse was forced to march his little butt off to class. As he navigated the stairs in his heels, his thoughts turned to Claire... and all the others in Home 23 who hadn't scored anywhere near as highly as him. He really should be more grateful of where he was in life. For the algorithm could just as easily have made him a 'Sally'.

Chapter 4: Start off with a Squeeze

"I wondered when it was going to be my turn..."

Fran beamed down at the sissy between her knees, shuffling herself forward a bit in her seat so he would have easier access. Silvertongue's lesson for the morning was 'Cunnilingus 101', so the assorted members of the class blessed with female paraphernalia were riding high. Lizzy was somewhere further down the line, giggling down at Suzy's unhesitant approach. Jesse had got the distinct impression that the other femboy was not best pleased about this arrangement of pairings, so was just trying to get the lesson done with as soon as possible. In fact he also found it a little odd that their little group had only seemed to be paired off together so far, while the rest of the class had been mixed around a lot more. Was this some other purposeful scheme of the Algorithm, testing the bounds of their new-found friendships... or just the coincidence of a truly randomised system?

Either way... Franceska, at least, seemed happy about her given partner.

"I've never actually had anyone girly down there before... It's always just cocks, cocks, cocks, slamming away... Even when they use their fingers or tongues, you know they're just viewing it as an extra sausage they've grown somewhere weird."